Thionyl Chloride → HCID 22161766, compound

HRID 1088790Notes

Reaction equation

HRID 1088790 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH2:12]O)[C:5]([CH3:14])=[CH:4][CH2:3]1.S(Cl)([Cl:17])=O>ClCCl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH2:12][Cl:17])[C:5]([CH3:14])=[CH:4][CH2:3]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22161782HCID 22161782, compound

Product 1

HCID 22161766HCID 22161766, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,4-Dimethyl-8-hydroxymethyl-1,2-dihydroquinoline (0.9 g) was dissolved in dichloromethane (30 ml). To this solution was added dropwise thionylchloride (0.6 g) with stirring under ice-cooling, and the mixture was stirred for 30 minutes. After completion of the reaction, dichloromethane was distilled off under reduced pressure, and n-hexane was added to the residue. The mixture was concentrated under reduced pressure to give 1,4-dimethyl-8-chloromethyl-1,2-dihydroquinoline (0.8 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 minutes
  3. distillationwas distilled off under reduced pressure, and n-hexane
  4. additionwas added to the residue
  5. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-64547586ac704c8a931a18cb0fa2f563
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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